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Метакриловая кислота структурированное изображение

Метакриловая кислота

  • английское имяMethacrylic acid
  • CAS №79-41-4
  • CBNumberCB9240023
  • ФормулаC4H6O2
  • мольный вес86.09
  • EINECS201-204-4
  • номер MDLMFCD00002651
  • файл Mol79-41-4.mol
химическое свойство
Температура плавления 12-16 °C (lit.)
Температура кипения 163 °C (lit.)
плотность 1.015 g/mL at 25 °C (lit.)
плотность пара >3 (vs air)
давление пара 1 mm Hg ( 20 °C)
показатель преломления n20/D 1.431(lit.)
Fp 170 °F
температура хранения Store at +15°C to +25°C.
растворимость Chloroform, Methanol (Slightly)
форма Liquid
пка pK1:4.66 (25°C)
цвет Clear
РН 2.0-2.2 (100g/l, H2O, 20℃)
Запах Repulsive
Вязкость 1.36mm2/s
Пределы взрываемости 1.6-8.7%(V)
Растворимость в воде 9.7 g/100 mL (20 ºC)
Чувствительный Moisture & Light Sensitive
Мерк 14,5941
БРН 1719937
Пределы воздействия TLV-TWA 20 ppm (~70 mg/m3) (ACGIH).
Стабильность May be stabilized by the addition of MEHQ (Hydroquinone methyl ether, ca. 250 ppm) or hydroquinone. In the absence of a stabilizer this material will readily polymerize. Combustible. Incompatible with strong oxidizing agents, hydrochloric acid.
ИнЧИКей CERQOIWHTDAKMF-UHFFFAOYSA-N
LogP 0.93 at 22℃
Непрямые добавки, используемые в веществах, контактирующих с пищевыми продуктами METHACRYLIC ACID
FDA 21 CFR 175.105; 177.1010; 178.3790
Справочник по базе данных CAS 79-41-4(CAS DataBase Reference)
Рейтинг продуктов питания EWG 2-5
FDA UNII 1CS02G8656
Справочник по химии NIST 2-Propenoic acid, 2-methyl-(79-41-4)
Система регистрации веществ EPA Methacrylic acid (79-41-4)
больше
Заявления об опасности и безопасности
Коды опасности C
Заявления о рисках 21/22-35-37-20/21/22
Заявления о безопасности 26-36/37/39-45
РИДАДР UN 2531 8/PG 2
OEB A
OEL TWA: 20 ppm (70 mg/m3) [skin]
WGK Германия 1
RTECS OZ2975000
Температура самовоспламенения 752 °F
TSCA Yes
кода HS 2916 13 00
Класс опасности 8
Группа упаковки II
Банк данных об опасных веществах 79-41-4(Hazardous Substances Data)
Токсичность LD50 orally in Rabbit: 1320 mg/kg
NFPA 704:
2
3 2

рисовальное письмо(GHS)

  • рисовальное письмо(GHS)

    GHS hazard pictogramsGHS hazard pictograms

  • сигнальный язык

    опасность

  • вредная бумага

    H335:Может вызывать раздражение верхних дыхательных путей.

    H302+H332:Вредно при проглатывании или при вдыхании.

    H314:При попадании на кожу и в глаза вызывает химические ожоги.

    H311:Токсично при попадании на кожу.

  • оператор предупредительных мер

    P261:Избегать вдыхания пыли/ дыма/ газа/ тумана/ паров/ аэрозолей.

    P280:Использовать перчатки/ средства защиты глаз/ лица.

    P301+P312:ПРИ ПРОГЛАТЫВАНИИ: Обратиться за медицинской помощью при плохом самочувствии.

    P303+P361+P353:ПРИ ПОПАДАНИИ НА КОЖУ (или волосы): Снять/удалить немедленно всю загрязненную одежду. Промыть кожу водой.

    P304+P340+P310:ПРИ ВДЫХАНИИ: Свежий воздух, покой. Немедленно обратиться за медицинской помощью.

    P305+P351+P338:ПРИ ПОПАДАНИИ В ГЛАЗА: Осторожно промыть глаза водой в течение нескольких минут. Снять контактные линзы, если Вы ими пользуетесь и если это легко сделать. Продолжить промывание глаз.

Метакриловая кислота химические свойства, назначение, производство

Описание

Methacrylic acid, abbreviated MAA, is an organic compound. This colourless, viscous liquid is a carboxylic acid with an acrid unpleasant odor. It is soluble in warm water and miscible with most organic solvents. Methacrylic acid is produced industrially on a large scale as a precursor to its esters, especially methyl methacrylate (MMA) and poly(methyl methacrylate) (PMMA). The methacrylates have numerous uses, most notably in the manufacture of polymers with trade names such as Lucite and Plexiglas. MAA occurs naturally in small amounts in the oil of Roman chamomile.

Химические свойства

Methacrylic acid is is a colorless, moderately volatile, corrosive liquid with a strongly acrid odor. It was first prepared in 1865 from ethyl methacrylate, in turn obtained by dehydration of ethyl α-hydroxyisobutyrate.

Использование

Methacrylic acid is used in the manufacture of methacrylate resins and plastics. It is used as Monomer for large-volume resins and polymers, organic synthesis. Many of the polymers are based on esters of the acid, as the methyl, butyl, or isobutyl esters. Methacrylic acid and methacrylate esters are used to prepare a wide range of polymers [→ Polyacrylamides and Poly(Acrylic Acids), → Polymethacrylates]. Poly(methyl methacrylate) is the primary polymer in this category, and it provides water-clear, tough plastics that are used in sheet form in glazing, signs, displays, and lighting panels.

Подготовка

The most common route for the preparation of methacrylic acid is from acetone as follows:

79-41-4 synthesis_1


In a typical process, acetone is treated with hydrogen cyanide at 140??C in the presence of ammonia as catalyst. The acetone cyanohydrin produced is treated with concentrated sulphuric acid at 100??C to form methacrylamide sulphate. This intermediate is not isolated but is directly converted to methacrylic acid by treatment with water at about 90??C.
A competitive route now in commercial operation involves the two stage oxidation of isobutene with air. The reaction proceeds via methacrolein:

79-41-4 synthesis_2

Методы производства

The most common approach to methacrylic acid synthesis is the hydrolysis of methacrylamide sulfate, obtained from acetone cyanohydrin. Methyl methacrylate may be prepared directly in a similar way by adding methanol in the final reaction step.
In the manufacture of methacrylic acid, methacrylamide sulfate is reacted with water under conditions similar to those used for formation of the ester. The reactor effluent separates into two phases. The upper organic layer is distilled to provide pure methacrylic acid. The lower layer is steam stripped to recover dilute aqueous methacrylic acid, which is recycled to the hydrolysis reactor. The waste acid stream is treated as in the manufacture of the ester.

Определение

ChEBI: Methacrylic acid is an alpha,beta-unsaturated monocarboxylic acid that is acrylic acid in which the hydrogen at position 2 is substituted by a methyl group. It is functionally related to an acrylic acid. It is a conjugate acid of a methacrylate.

Общее описание

Methacrylic acid appears as a clear colorless liquid (or low-melting solid) with a pungent odor. Corrosive to metals and tissue. Flash point 170°F. Melting point 61°F. May polymerize exothermically if heated or contaminated. If the polymerization takes place inside a container, the container may rupture violently. Less dense than water. Vapors heavier than air. Used to make plastics.

Реакции воздуха и воды

Soluble in water.

Профиль реактивности

Methacrylic acid reacts with strong oxidizing agents. Presents a storage hazard: violent exothermic polymerizations leading to explosion can occur spontaneously, particularly at low inhibitor or stabilizer concentrations [Anon., CISHC Chem. Safety Summ., 1979, 50, p. 34; Bond, J., Loss Prev. Bull., 1991, 101, p. 1].

Угроза здоровью

Methacrylic acid is a highly corrosive liquid.Contact with eyes can result in blindness.Skin contact may produce burns. No inhalation toxicity was observed in rats. Exposureto its vapors may produce skin and eye irritation, which can be mild to moderate. Adermal LD50 value in rabbits is 500 mg/kg.

Пожароопасность

Combustible liquid; flash point (open cup) 76°C (170°F); vapor pressure <0.1 torr at 20°C (68°F). Fire-extinguishing agent: water spray, “alcohol” foam, dry chemical, or CO2; use a water spray to dilute and flush the spill and to disperse the vapors.
Methacrylic acid polymerizes readily. The reaction is exothermic. The rate of reaction accelerates on heating, which may result in violent rupture of closed containers. The polymerization may be inhibited with a trace quantity of hydroquinone and hydroquinone monomethyl ether (Aldrich 2006). The acid may be stored safely below its melting point.

Профиль безопасности

Poison by intraperitoneal route. Moderately toxic by ingestion and skin contact. Corrosive to skin, eyes, and mucous membranes. Mutation data reported. Flammable when exposed to heat, flame, or oxidizers. A storage hazard; exothermic polymerization may occur spontaneously. To fight fire, use alcohol foam, spray, mist, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.

Возможный контакт

Methacrylic acid is used in preparation of methacrylates and carboxylated polymers; in the production of the material or its alkyl esters, as monomers or comonomers for synthetic resins for the production of plastic sheets, moldings, and fibers.

Канцерогенность

Methacrylic acid was considered by the IARC Working Groups, but monographs were not prepared because adequate data on its carcinogenicity were not available. The IUCLID database reports a dermal application study (dose unspecified) of mice treated three times per week for 4 months and then observed for their lifetimes. No excess dermal tumors were observed.

Перевозки

UN2531 Methacrylic acid, stabilized, Hazard class: 8; Labels: 8-Corrosive material.

Методы очистки

Aqueous methacrylic acid (90%) is saturated with NaCl (to remove the bulk of the water), then the organic phase is dried with CaCl2 and distilled under vacuum. Polymerisation inhibitors should be added to the distillate and include 0.25% p-methoxyphenol, 0.1% hydroquinone, or 0.05% N,N'-diphenyl-p-phenylenediamine. [Beilstein 2 IV 1518.]

Несовместимости

Vapor may form explosive mixture with air. A reducing agent; incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Aqueous solution is strongly acidic: incompatible with strong acids; caustics, ammonia, amines, isocyanates, alkylene oxides; epichlorohydrin. Will polymerize readily from heating above 59F/15C, or due to the presence of light, oxidizers (e.g., peroxides); or in the presence of traces of hydrochloric acid, with fire or explosion hazard. Attacks metals. Note: Typically contains 100 ppm of monomethyl ether hydroquinone (150-76-5) as an inhibitor to prevent polymerization

Утилизация отходов

Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.

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